Potassium Carbonate → HCID 68751488, 화합물

HRID 1038839

반응식

HRID 1038839 반응식
Cl[C:2]1[N:3]=[C:4]([NH:11][CH:12]2[CH2:14][CH2:13]2)[C:5]2[O:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[CH3:15][S:16]([C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1)(=[O:18])=[O:17].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C([O-])([O-])=O.[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC(O)(C)C>[CH2:12]([NH:11][C:4]1[C:5]2[O:10][CH:9]=[CH:8][C:6]=2[N:7]=[C:2]([NH:23][C:22]2[CH:21]=[CH:20][C:19]([S:16]([CH3:15])(=[O:18])=[O:17])=[CH:25][CH:24]=2)[N:3]=1)[CH:14]=[CH2:13]

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 796174-(Methylsulfonyl)anilineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 866650932-chloro-N-cyclopropylfuro[3,2-d]pyrimidin-4-amine

생성물 1

HCID 68751488HCID 68751488, 화합물수율 27.8%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 6386tert-Butanol용매

반응 조건

온도
100 °C

실험 절차

A vial was charged with 2-chloro-N-cyclopropylfuro[3,2-d]pyrimidin-4-amine (0.09 g, 0.429 mmol, Preparation #A.1), 4-(methylsulfonyl)aniline (0.077 g, 0.451 mmol, Oakwood), X-Phos (0.020 g, 0.043 mmol), Pd2dba3 (0.020 g, 0.021 mmol), K2CO3 (0.062 g, 0.451 mmol) and t-BuOH (3.5 mL). The vial was purged with argon and heated at about 100° C. overnight. The mixture was diluted with CHCl3 (about 10 mL) passed through a SiCO3 SPE cartridge and concentrated. The crude product was purified by preparative reverse phase HPLC (Table 2, Method a) to provide N4-allyl-N2-(4-(methylsulfonyl)phenyl)furo[3,2-d]pyrimidine-2,4-diamine (0.041 g, 27%): 1H NMR (DMSO-d6) δ 9.53 (s, 1H), 8.11 (d, J=2.1 Hz, 1H), 8.02 (m, 3H), 7.72 (d, J=8.9 Hz, 2H), 6.80 (d, J=2.1 Hz, 1H), 6.00 (ddd, J=17.1, 10.2, 5.1 Hz, 1H), 5.22 (dd, J=17.1, 1.6 Hz, 1H), 5.11 (dd, J=10.5, 1.6 Hz, 1H), 4.14 (dd, J=5.1 Hz, 2H), 3.11 (s, 3H). Syk IC50=B.

후처리

  1. customThe vial was purged with argon
  2. additionThe mixture was diluted with CHCl3 (about 10 mL)
  3. concentrationconcentrated
  4. customThe crude product was purified by preparative reverse phase HPLC (Table 2, Method a)

출처 및 근거

ORD 기록
ord-073ca5a0a38f4c1599ce3e0d5c1fe0e7
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08551981B2

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